Synthesis of 2-Aryl-5-styrylphospholes:  Promising Candidates for the Phosphole-Based NLO Chromophores

• Published in: Journal of organic chemistry Vol. 72; no. 16; pp. 6200 - 6205
• Main Authors: Matano, Yoshihiro, Miyajima, Tooru, Imahori, Hiroshi, Kimura, Yoshifumi
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 03-08-2007
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Exact sciences and technology; Noncondensed benzenic compounds; Organic chemistry; Preparations and properties; Rayleigh scattering; Polarizability; Organic phosphine; Non linear optics; Ground state; Stilbene derivatives; Fluorescence spectrometry; Chlorine Organic compounds; Optical properties; Benzenic compound; Aromatic compound; Conjugated compound; Diynic compound; Chemical synthesis; Ethylenic compound; Chromophore; Excited state; Ultraviolet visible spectrometry
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo070822f

2-Aryl-1-phenyl-5-styrylphospholes were prepared in good yields in a one-pot procedure from the corresponding 1,9-diarylnona-8-ene-1,6-diynes and dichloro(phenyl)phosphine via intermediary titanacyclopentadienes. According to the UV−vis absorption and fluorescence spectra of this class of compounds, the optical properties of the phosphole−vinylene-bridged π-conjugated system have been revealed to depend strongly on the electronic character of the terminal functionalities. In particular, the polarizability at the excited-state has been found to be considerably greater than that in the ground state. High molecular hyperpolarizabilities obtained for the push−pull type of 2-aryl-5-styrylphospholes in the hyper-Rayleigh scattering measurements demonstrate the potential utility of the stilbene-type phosphole derivatives as a new class of second-order NLO chromophores.